Claims
- 1. A compound of the formula ##STR11## wherein R.sup.1 is alkyl having from 1 to 8 carbon atoms or benzyl
- R.sup.2 is a hydrogen atom, alkyl having from 1 to 3 carbon atoms or benzyl;
- R.sup.3 is a hydrogen atom, halo having an atomic weight of from about 19 to 80, alkyl having from 1 to 3 carbon atoms, or alkoxy having from 1 to 3 carbon atoms;
- A is the residue of an unsaturated long-chain fatty acid minus the carboxylic portion, said acid having from 8 to 24 carbon atoms and having from 1 to 4 ethylenically unsaturated positions.
- 2. A compound of claim 1 in which A is of either the types (A1) having the structure:
- CH.sub.3 --(CH.sub.2).sub.f --(CH.dbd.CH).sub.g --(CH.sub.2).sub.h ; or
- (A2) having the structure
- CH.sub.3 --(CH.sub.2).sub.n --(CH.dbd.CH--CH.sub.2).sub.m (CH.sub.2).sub.p
- in which f is a whole integer of from 1 to 10, g is a whole integer of from 1 to 4, and h is a whole integer of from 4 to 9;
- n is a whole integer of from 1 to 4,
- m is a whole integer of from 2 to 4,
- and p is a whole integer of from 2 to 7.
- 3. A compound of claim 2 in which A is of type (A1).
- 4. A compound of claim 3 in which A is the residue of oleic acid.
- 5. A compound of claim 3 in which A is the residue of palmitoleic acid.
- 6. A compound of claim 2 in which A is of type (A2).
- 7. A compound of claim 6 in which A is the residue of linoleic acid.
- 8. A compound of claim 6 in which A is the residue of linolenic acid.
- 9. A compound of claim 1 in which R.sup.2 is a hydrogen atom.
- 10. A compound of claim 1 in which R.sup.3 is a hydrogen atom.
- 11. A compound of claim 1 in which R.sup.1 is ethyl.
- 12. The compound of claim 1 which is .alpha.-[(1-oxo-9, 12-octadecadienylamino)]-1H-indole-3-propanoic acid, ethyl ester (cis, cis isomer).
- 13. The compound of claim 1 which is .alpha.-[(1-oxo-9octadecenylamino)]-1H-indole-3-propanoic acid, ethyl ester (cis isomer).
- 14. A method of controlling the cholesterol ester content of an arterial wall, in a mammal in need of such treatment, comprising orally administering a cholesterol ester-controlling amount of a compound of claim 1 to said mammal.
- 15. A pharmaceutical composition suitable for controlling the cholesterol ester content of an arterial wall of a mammal comprising a cholesterol ester-controlling effective amount of a compound of claim 1 and a nontoxic pharmaceutically-acceptable carrier.
- 16. A composition of claim 15 in solid form.
- 17. A composition of claim 15, in which the compound is present in an amount of from about 25 to 2,500 milligrams.
- 18. A composition of claim 16 in which the compound is .alpha.-[(1-oxo-9-octadecenylamino)]-1H-indole-3-propanoic acid, ethyl ester (cis isomer).
- 19. The compound of claim 1 which is .alpha.-[(1-oxo-9,12-octadecadienylamino)]-1H-indole-3-propanoic acid, n-octyl ester (cis,cis isomer).
- 20. The compound of claim 1 which is .alpha.-[(1-oxo-9,12-octadecadienylamino)]-1H-indole-3-propanoic acid, benzyl ester (cis,cis isomer).
- 21. A compound of claim 1 in which each unsaturated position of A is in the cis-type isomeric form.
- 22. The compound of claim 1 which is 2-(1oxo-9-octadecenylamino)-3-(1-methylindolyl)-propanoic acid, ethyl ester (cis isomer).
- 23. The compound of claim 1 which is 2-(1oxo-9-octadecenylamino)-3-(1H-5-methoxyindolyl)-propanoic acid, ethyl ester (cis isomer).
- 24. A method of claim 14 in which the compound is administered at a daily dosage of from about 100 milligrams to about 5,000 milligrams.
- 25. A method of claim 14 in which the compound is administered at a daily dosage of from about 100 milligrams to about 15,000 milligrams.
- 26. A method of claim 14 in which the compound is .alpha.-[(1oxo-9-octadecenylamino]1H-indole-3-propanoic acid, ethyl ester (cis isomer).
- 27. A compound of claim 1 in which R.sup.3 is fluoro or chloro.
- 28. A compound of claim 1 in which R.sup.1 is unbranched.
- 29. A compound of claim 1 in which A has an odd number of carbon atoms.
- 30. A compound of claim 1 in which R.sup.1 is ethyl.
Parent Case Info
This is a continuation-in-part of copending application Ser. No. 5,355 filed Jan. 22, 1979, which in turn is a continuation-in-part of then copending application Ser. No. 867,813 filed Jan. 9, 1978 (both now abandoned).
Foreign Referenced Citations (2)
Number |
Date |
Country |
40-9134 |
May 1965 |
JPX |
40-10571 |
May 1965 |
JPX |
Non-Patent Literature Citations (1)
Entry |
Suyama et al., "Chem Abst.", 66, Abst. 29058y (1967) of Yakugaku Zasshi 86(10) pp. 967-972 (1966). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
5355 |
Jan 1979 |
|
Parent |
867813 |
Jan 1978 |
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